For six seasons, the ladies of Sex and the city provided her fans with complex relationships, laughter, heartache, and some really good fashion choices. It also provided some of the best scenes that will live for free in fans ‘heads for years to come, and while some involve the series’ best relationships, there are others that feature some of Carrie Bradshaw’s most questionable adventures.

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Some of the best episodes involve these Mr. Wrongs and the situations in which Carrie Bradshaw (Sarah Jessica Parker) messes with them. Everyone has their own quirks, but these guys are on a whole different level.

10 “The Man Who Steals Cheap Used Books For No Reason”: Season 2, Episode 3

Carrie Bradshaw has been on many dates during the Sex and the city series, but in the episode, “The Freak Show,” she ponders the idea that all the men in town could be “freaks.” Carrie has a trio of dates throughout the episode, and one of them turns out to be a perfectly capable man who decides to steal things just for the sake of doing it. This could be giving insight into a deeper problem and Carrie realizes.

She decides that everyone can have a little “freak” after stopping by another date’s apartment looking for a flaw that isn’t there.

9 Willie Applegate: Season 6, Episode 1

Carrie having lunch outside with Will

Despite Carrie going on a date with fellow writer Jack Berger, she attempts to date someone “simultaneously” after getting advice from the girls. He meets Willie Applegate, played by Wallace Langham, a seemingly nice man, but his nerves and obsession with a possible eye stye make him act extremely uncomfortable.

What follows is a series of uncomfortable events, such as Wallace getting balsamic vinegar in his eye and a pigeon landing on his head. It’s safe to say that this is one of Carrie’s more awkward quotes. At this point, Carrie might be better off dating someone she really wants to date, rather than exposing herself just so she can date multiple people at the same time.

8 Gilles: Season 1, Episode 5

Carrie walking outside with her date

While doing some cardio, aka “shopping” for Carrie, she runs into her friend Amalita and her new boyfriend. Amalita’s life is extravagant with travels and rich men, and while in town he invites her to dinner. Later, Carrie meets an architect named Gillies, to whom she is immediately attracted. She decides to spend the night with him at his hotel, and after a fun-filled night, he wakes up to find that Gilles is gone and a lot of money remains in his place.

Apparently Amalita is a sex worker and Gilles assumed that Carrie was too. It could have been a miscommunication, but it was still incredibly shocking for Carrie to wake up to it.

7 “The Man with Two Faces”: Season 2, Episode 3

Carrie queuing up with her date while watching him

Going back to the episode, “The Freak Show”, quote no. Carrie’s # 2 (James Joseph O’Neil) seemed like a nice guy who liked Carrie, but one wrong move and it gets him going, which is not a good sign.

Carrie tries this for the first time and for the last time when they are in line waiting for the movie. When Date # 2 senses that the man behind him is listening to their conversation, he loses his cool. Everybody has bad days, but this may be a path Carrie doesn’t want to follow.

6 Howie Halberstein: Season 6, Episode 8

Carrie at a wedding date kissing her hand

Weddings are the place for singles to mingle with each other and perhaps find love themselves. Unfortunately for Carrie, this was not her day. As her friend Charlotte (Kristin Davis) prepares to marry her second husband, Carrie meets Howie Halberstein (Bryan Callen).

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After Howie and Carrie get to know each other more after rehearsal dinner, things don’t go as planned. Howie’s intimacy skills are too fast for Carrie, and she ends up hurting her back. At the next day’s wedding, Carrie tells Howie that she’s not that interested, and Howie doesn’t take it well. After shooting daggers at her all day with her eyes, Carrie realized she dodged a bullet … but not fast enough.

5 Ray King – Season 4, Episode 3

Carrie's date looks at her while she looks away

In a friendly outing with Mr. Big (Chris Noth), Carrie catches the eye of jazz musician Ray King (Craig Bierko). Despite Mr. Big trying to intervene, Carrie and Ray end up having a brief romance. Ray is kind enough and he and Carrie have intense chemistry, but that’s about it.

They have nothing in common with each other, and their attention span was everywhere and anywhere, meaning the relationship could never last or get anywhere serious. This was a bummer because there was the potential for Carrie to finally leave her messy relationship with Big behind for good.

4 Wade Adams: Season 3, Episode 15

Carrie looking at the date at the comic book store

The women of Sex and the city They are known to have dated a fair number of men (and women) their age or older, and when Carrie takes an interest in Wade Adams (Cane Peterson), aka “Superboy,” her interest shifts to younger men. . Carrie doesn’t mind because she wants a fun-filled romance with the comic book store worker, which involves hanging out around New York City and even drinking some marijuana.

Carrie discovers that Wade lives with his parents, and when they get caught by their mother with marijuana, Wade shows his age by blaming Carrie for bringing it in. Maybe feeling young again is not all that is advertised, and although Carrie had to leave Wade, she decided to take “her” marijuana with her, which can be considered grade A karma.

3 Keith Travers: Season 3, Episode 14

Carrie kissing keith travers in mansion

Vince Vaughn is known for his comedic roles in films, such as Wedding crashers Y Couples retreat, but before all that, he appeared as a guest star in the episode “Sex in another city”. Vince played Keith Travers, a man Carrie meets in Los Angeles, after traveling there with the girls. Keith leaves Carrie speechless after being turned away from an after-movie premiere party and tells her that he is Matt Damon’s agent.

Of course, Keith isn’t all that he seems, and while he and Carrie hang out at his “mansion,” the real owner, Carrie Fisher, breaks up the party and reveals her true identity. Keith takes care of her house and has made his way into Carrie’s arms. Oh. Although the adventure did not work out, it was one of the best Sex and the city episodes that did not take place in New York City.

two Seth Robinson: Season 2, Episode 13

Carrie kissing her date in her apartment

It’s always interesting when a musician moves into the acting world, and when Jon Bon Jovi decides to jump into an episode of Sex and the city as a guest star, he was questionable, to say the least. But it wasn’t that the “Living on a Prayer” singer failed, but rather what his character did, that was the problem.

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As Carrie continues to get over her breakup with Mr. Big, her friends recommend therapy because she’s clearly not getting better. In the waiting room, he meets Seth Robinson, played by Jon Bon Jovi. At first, Seth seems like the perfect match, but when he tells Carrie to leave the girls after being intimate, she immediately realizes that this is not the guy she can settle with. In this Sex and the city Dating accident, Carrie could have used a bit of Miranda’s tough love advice.

1 Bill Kelley: Season 3, Episode 2

Carrie and her date sitting on the steps talking

Carrie and the girls visit Staten Island in the episode, “Where There’s Smoke …”, where Carrie is on the jury to judge the finalists for the New York Fire Department’s annual men’s calendar. While judging, he meets Bill Kelley, played by John Slattery. He seems like the perfect catch – he’s handsome, rich, and attracted to Carrie.

After weeks of the relationship going well, he finally asks her for a sexual favor that makes her think twice. The request leaves Carrie speechless and unable to commit. For such a good catch, it was a terrible disappointment for her.

NEXT: Sex and the City Revival: 10 Things We Hope To See For Carrie

10 non-traditional TV romances that aren't afraid to break the rules

10 non-traditional TV romances that aren’t afraid to break the “rules”

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